Ben Thompson bopped around doing engineer things at Apple, Microsoft, and Automattic, until more than a decade ago he started this subscription newsletter with business-of-tech kind of analysis. The success of his paid newsletter gave Substack the idea [0].

A fair chunk of the tech who’s-who seem to find his thinking useful.

[0] https://www.vox.com/2017/10/16/16480782/substack-subscriptio...